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Steroid compounds with endothelin receptor A antagonistic activity and intermediate thereof

A compound and steroid technology, applied in the field of new steroid compounds and their intermediates, can solve the problems of long synthetic routes and complicated processes

Inactive Publication Date: 2009-07-08
JIANGSU SIMCERE PHARMACEUTICAL R & D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This triterpenoid is a rare 13-hydroxymethyl compound in nature. Myriceric Acid A has been patented through biosynthesis and chemical synthesis. The synthesis route is long and complicated.

Method used

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  • Steroid compounds with endothelin receptor A antagonistic activity and intermediate thereof
  • Steroid compounds with endothelin receptor A antagonistic activity and intermediate thereof
  • Steroid compounds with endothelin receptor A antagonistic activity and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013]

[0014] Synthesis of Acetyl Diosgenin:

[0015] Diosgenin (5.00 g, 12.1 mmol) was dissolved in 60 mL of pyridine, 7.2 mL of acetic anhydride and 0.5 g of DMAP were added with stirring, and stirring was continued at room temperature for 4.5 hours. Pour the reaction solution into 300mL of ice water under stirring, continue to stir for 10 minutes and then filter with suction, wash repeatedly with appropriate amount of water to remove pyridine as much as possible, and dry to constant weight under infrared light to obtain 5.40g of white solid (R f =0.70, ethyl acetate:n-hexane=1:4), the yield was 98%.

[0016] ESI-MS(+): m / z 479[M+Na] + .

[0017] 3β-Acetoxy-5,6-epoxydiosgenin

[0018] Acetyldiosgenin (2.74g, 6mmol) was dissolved in 30mL of chloroform, m-CPBA (1.58g, 9mmol) was added with stirring, and stirring was continued at room temperature for 5 hours, during which the reaction system changed from clear to white turbid. After the reaction stopped, 30 mL of chlor...

Embodiment 2

[0033]

[0034] Acetyl dehydroepiandrosterone

[0035] Method 1: Dissolve dehydroepiandrosterone (1.44g, 5mmol) in 15mL of dichloromethane, add 1.2mL of pyridine, 1mL of acetic anhydride and 60mg of N,N'-dimethylaminopyridine (DMAP) under stirring, Stirring was continued for 12 hours. Wash with dilute hydrochloric acid (2 times the equivalent of pyridine) under ice-cooling conditions. The organic phase was washed successively with 15 mL of water, 15 mL of 10% sodium bicarbonate solution, and 15 mL of water, and the obtained aqueous phase was washed with 5 mL of dichloromethane, and the organic phases were combined. After the solvent was removed by rotary evaporation, the obtained white solid was washed with n-hexane to obtain 1.22 g of white solid, with a yield of 74.0%.

[0036] Method 2: Dissolve dehydroepiandrosterone (2.88 g, 10 mmol) in 40 mL of pyridine, add 6 mL of acetic anhydride and 120 mg of DMAP under stirring, and continue stirring at room temperature for 4.5...

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PUM

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Abstract

The invention provides a structure and a synthetic method thereof. The structure is obtained by modifying structures such as yam steroid sapogenin, proluton, dehydroepihydro-ketone and the like, and has an endothelin receptor A antagonistic active compound.

Description

technical field [0001] The invention belongs to the field of chemistry, and relates to new steroidal compounds with endothelin receptor A antagonistic activity and intermediates thereof. Background technique [0002] Stroke is a kind of acute cerebrovascular disease with sudden onset, which seriously threatens human life. There are 2 million new strokes in my country every year, and it is estimated that the annual cost of stroke treatment is about 24 billion yuan. Endothelin is a strong vasoconstrictor substance that binds to ETA receptors to mediate vasoconstriction. After brain trauma, the application of ETA receptor antagonists can improve the blood supply of cerebral vessels and prevent ischemic stroke. [0003] Myriceric Acid A is a natural product with endothelin receptor A antagonist activity isolated from the plant wild bayberry (Myrica cerifera) in 1996. It has been improved to S-0139 by Shionogi Company. As an endothelin receptor A antagonist, it has been Conduc...

Claims

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Application Information

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IPC IPC(8): C07J21/00C07J7/00C07J3/00C07J1/00A61K31/58A61K31/57A61K31/56A61K31/5685A61P43/00
Inventor 巨勇吴迪矛陈向纯檀爱民华垚袁云霞王冬春
Owner JIANGSU SIMCERE PHARMACEUTICAL R & D CO LTD
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